Potassium Carbonate → Bisindolylmaleimide I

HRID 1769226Notes

Reaction equation

HRID 1769226 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]2[C:18]([N:20](C)[C:21](=[O:38])[C:22]=2[C:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]([CH2:32][CH2:33][CH2:34][N:35]([CH3:37])[CH3:36])[CH:24]=2)=[O:19])=[CH:9]1)=O)(C)(C)C.C(OC(N1C2C(=CC=CC=2)C(C2C(N(C)C(=O)C=2C2C3C(=CC=CC=3)NC=2)=O)=C1)=O)(C)(C)C.C(=O)([O-])[O-].[K+].[K+].CN(C)CCCCl>CC(C)=O.O>[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]2[C:18]([NH:20][C:21](=[O:38])[C:22]=2[C:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]([CH2:32][CH2:33][CH2:34][N:35]([CH3:37])[CH3:36])[CH:24]=2)=[O:19])=[CH:9]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 11166603HCID 11166603, compoundHCID 22410303HCID 22410303, compound

Product 1

HCID 2396Bisindolylmaleimide I

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

The 2-(1-tert. -butoxycarbonyl-1H-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-1H-indol-3-yl]-N-methylmaleinimide used as starting material is prepared as follows: A mixture of 0.9 g (2.03 mmol) 2-(1-tert.-butoxycarbonyl-1H-indol-3-yl)-3-(1H-indol-3-yl)-N-methylmaleinimide (Tetrahedron, 44, 2887/1988), 0,3 g potassium carbonate and 0.3 g (2.4 mmol) 3-dimethylaminopropyl chloride in 10 ml acetone is stirred for 12 hours at ambient temperature and for 8 hours under reflux. After cooling, the reaction mixture is poured into water and extracted with ethyl acetate. The red extract is evaporated and the residue flash chromatographed on silica gel (Merck Type 7734) using, as elution agent, a mixture of toluene/ethanol (10+1.5 v/v). The desired product is obtained in the form of a red oil and used as such in the above reaction. Yield 0.8 g (74% of theory); RF=0,20 (toluene/ethanol 1:2 v/v).

Workup

  1. customis prepared
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate
  5. extractionThe red extract
  6. customis evaporated
  7. customthe residue flash chromatographed on silica gel (Merck Type 7734)
  8. washusing, as elution agent
  9. additiona mixture of toluene/ethanol (10+1.5 v/v)

Sources & evidence

ORD record
ord-d59876bdb2a14892b92ff57d4688c8b5
Source dataset
uspto-grants-1995_01
Patent number
US05380746

Reaction notes

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